


James Spader, Eat Your Heart Out

by dastiel_gal (rock_chick)



Series: Secretary [1]
Category: Supernatural RPF
Genre: Alternate Universe - Gender Changes, F/M, Trans Female Character
Language: English
Status: Completed
Published: 2010-07-20
Updated: 2010-07-20
Packaged: 2017-10-24 06:50:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,633
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/260344
Author URL: https://archiveofourown.org/users/rock_chick/pseuds/dastiel_gal
Summary: <blockquote class="userstuff">
              <p>Jeff and Jared get assigned a hot new secretary.  They <i>both</i> want her, and it looks like she's a pricktease to boot.  (Pre-op trans Jensen)</p>
            </blockquote>





	James Spader, Eat Your Heart Out

**Author's Note:**

> Written for the prompt [**JDM/Jared/Jensen - crossdressing, corsets, bondage, dirty talk, rough sex, plugs, double penetration**](http://community.livejournal.com/blindfold_spn/2172.html?thread=2153084#t2153084) in . It came out a lot crackier than intended, but the prompter loves it anyway, so yay me! I missed a couple of parts of the kink prompt (although I did get in every single point of the three-paragraph-long backstory she gave me *fistpump*). Other than that, I have no excuses, and I don't know what the fuck possessed me. Errrmmm.

"My stuff comes first, man. I have seniority."

"Screw you, Jeff, you know we're not really talking about work, here. I'm younger, better looking, and way more built. Jenny ain't even gonna look at you."

Jeff snorts at Padalecki's youthful bravado, brags right back about women going for experience, but he's not feeling quite as cocky as he sounds. The lad is _ripped_ , after all, even if he's a level or two under Jeff, and their brand new secretary is smokin'. Damn cutbacks, any other time he'd've got the hot secretary all to himself, never mind having to share her with an up-and-coming pipsqueak. He bites back a snarl. At least they'd beaten off the challenge from Edlund, who wanted to poach the new girl and foist his old battleaxe off on them.

\--oo00oo--

  
Jenny is luscious today. She's wearing cherry-red lipgloss, which just emphasizes a full, pouty mouth that really didn't need any emphasis to turn heads. And she keeps licking her lips.

"Maybe it's toffee-flavoured," says Jared.

"I'd lick it off for her," grins Jeff.

Not if Jared gets there first.

\--oo00oo--

  
They're supposed to be discussing the quarterly figures, but really they're surreptitiously ogling Jenny through the glass divider between Jeff's office and the secretary station, which is their new favourite pastime.

"She's working it. She's _gotta_ be," whines Jared, shifting in his seat. "Nobody sucks their pen like that by accident!"

Jeff's not so sure. If it's deliberate, it's subtle. Yeah, Jenny really does suck a pen fit to make a grown man cry... or sneak off to the executive bathroom for a little quiet time, at any rate. And then there's the constant lip-licking, and gnawing on her full bottom lip when she's nervous, and (oh, God) the way the tip of her tongue curls out of the corner of her mouth when she's concentrating. Jeff might have a small obsession with Jenny's gorgeous mouth.

"I dunno," he says. "I've never seen her sneak a look to see how we're taking it. Might be accidental."

Jenny has just gone over to the filing cabinet and bent over to open the bottom drawer, and holy fucking _Christ_ , her ass is perfect like that. They both stare, Jared slack-jawed and Jeff grinning wolfishly. And then, as Jenny straightens, she looks over her shoulder and catches them in the act. Her mouth drops open, which is no better for Jeff's sanity, and for a second they're all frozen in place. Then Jared blushes scarlet and ducks his head; Jeff, asshole that he is, just carries on looking until she scuttles back behind her desk, a little pinker than usual.

\--oo00oo--

  
Jenny's taken to wearing an above-the-knee skirt. Jeff and Jared have taken to dropping things when they go to her desk, just for the pleasure of watching her crouch in front of them, skirt creeping higher, and asking her to get files from the cabinet (S-Z, of course, bottom drawer) so they can admire her pert backside as she bends.

\--oo00oo--

  
There's now a $100 bet riding on whether or not Jenny is working them up for shits and giggles. Whenever Jeff and Jared are in the office on their own, she sucks her pen, and bends from the hips to pick things up, ass in the air; but when Jeff's in there with Edlund or Gamble, there's no pen-sucking, and picking things up happens with knees bent, thighs tight together and angled demurely sideways. Jeff isn't telling Jared that, nossir. Not till after payday, anyhow.

\--oo00oo--

  
While handing them their agendas, Jenny leans over the desk way further than is strictly necessary, giving the pair of them a flash of hot-pink lace down the cleavage of her shirt. Jared pops a boner, five minutes before a meeting with _clients_ , dammit, and is so embarrassed about it that he doesn't say a word to Jeff. About the cleavage, _or_ the bet.

\--oo00oo--

  
Today's skirt is even shorter, and Jenny - without any input from them - goes to fetch a file from the bottom drawer. Her legs are as amazing as the rest of her, and she's wearing stockings. _Lace-topped_ stockings, with a hint of smooth creamy skin visible just above. Jared damn near chokes to death on his coffee, and Jeff gets out his wallet without a word. She turns just in time to see the money change hands, and that adorable little pink blush makes another appearance.

\--oo00oo--

  
She's flat-out torturing the pair of them. Today's ensemble, as well as the short skirt, the unbuttoned cleavage and the lace-topped stockings they have come to expect, includes a pair of "fuck-me shoes" (Jeff's phrase) with spike heels and bright red undersoles. She's obviously not used to quite such high heels, and it gives a coltish wobble to her movements that is deliciously enticing.

"She's gonna be the death of me," groans Jeff.

"Guh," agrees Jared.

\--oo00oo--

  
Carver's secretary has been off sick all week, so Jenny has been asked to take the minutes for the late board meeting. She turned up this morning in an outfit ostensibly much more staid than usual, long skirt and blouse high in the neck, hair in a bun and glasses on. Jeff's disappointed until he realizes that it's a hobble skirt, in which she can only take tiny steps, and the whole outfit has such a kinky-librarian vibe that the pair of them are sporting semis for most of the day.

\--oo00oo--

  
When they get to the boardroom, she positions her chair at the side of the room in a spot clearly visible to Jeff and Jared, then spends most of the meeting crossing and uncrossing her ankles, sucking her pen top, glancing up at them over the top of her glasses, and squirming in her seat. By the time they get back to Jeff's office, Jared is a speechless mess of unsatisfied lust, Jeff is two steps from apoplexy, and Jenny? Jenny is calm and collected, wiggling her way into the room for all the world like she didn't just spend two hours (hell, two _months_ ) deliberately driving them insane. Jeff has _had_ it with this little scenario.

"Hey, Jenny," he drawls, shutting the door behind them and closing the blinds, "have you ever seen 'Secretary'?"

Jenny stops dead, a deep blush spreading across her face, and oh, she is _busted_.

"I was wondering, because you look _just_ like Maggie Gyllenhaal in that get-up."

That plush bottom lip is caught between Jenny's teeth again, she peeps up at Jeff over the top of the glasses, then sideways at Jared, and now he's certain that she wants them to take this further. She's just been waiting for them to get with the programme.

"Lean forward over the desk, Miss Ackles," growls Jeff. "It's time for your performance review."

\--oo00oo--

  
"What do you _mean,_ she's not a she?" Jared gawps at Jeff across the desk. He's been standing on the other side of it, holding Jenny's arms while Jeff spanked her. The whole thing has been exciting him wildly up to now, what with Jeff unzipping Jenny's skirt and letting it slither down to pool around her ankles, and the neverending legs and the luscious ass encased in black lace, and the spanking (Christ, how does Jeff _dare_ , they are so gonna get fired if she files a complaint!) and the desperate, needy little gasps Jenny has been making, but now he feels like he just had a bucket of cold water thrown over him.

"I mean, she has a penis. _He_ has a penis. I just copped a feel, and there it was."

Jenny is so red she couldn't get any redder, and is trying to bury her face in her shoulder.

"Don't worry about it, sweetheart," beams Jeff, "I swing both ways."

\--oo00oo--

  
Jared doesn't swing both ways - or at least, he didn't _think_ he did - so he takes some persuading, but in the end Jeff prevails by sitting Jenny in her wheelie-chair, lashing her wrists to the back with his tie, and rolling her up to Jared with an evil grin.

"Open wide, Jenny. Jared, man, what are you waiting for? Pants unzipped. _Blowjob._ "

Turns out Jared has a teensy bondage kink. Besides, who the hell could hold out long against a sweet proposition like a blowjob from Jenny's beautiful glossy mouth? And wow, the girl has a talented tongue.

\--oo00oo--

  
Apparently, Jenny sucked Jared's brains clean out through his dick, because he doesn't run away even when Jeff starts stripping Jenny's blouse off, and it becomes unavoidably obvious that the satin corset (Corset! Guh.) is padded out over a flat male chest, and that there is a hard cock straining to get out of the lacy knickers. He's feeling a little befuddled, actually, enough so that after watching Jeff slip off Jenny's panties and open her up with the lube she just happened to have in her handbag (naughty girl!), he's hard again, and when Jeff tells him to fuck her, and she flutters her eyelashes up at him and breathes, " _Please,_ Jared," he doesn't hesitate. He is _so_ going to hell.

\--oo00oo--

  
Jeff thinks all his birthdays came at once. He's sat in his desk chair, being given mind-blowing head by his secretary while his friend fucks her from behind. He's giving all the orders (yes, he's a top, _and?_ ), he has two delightfully attractive subordinates (submissives?) who are busy proving that they will do just about anything he demands of them, and they're all going to be right back here again tomorrow morning for more fun and games. His work-life balance just got irredeemably skewed in favour of the office. This does not suck. Or, well, not like Jenny sucks.

Maybe he'll tell her to leave the panties at home tomorrow.


End file.
